Cyclopropylamine → HCID 89783319, compound

Participants

Reaction Conditions

Reaction Steps

Prepared according to Example 131 using 2′-(3-fluoro-2-methyl-5-quinoxalinyl)-5′,6′-dihydrospiro[cyclopropane-1,7′-pyrrolo[3,2-c]pyridin]-4′(1′H)-one (Ex. 77a; 39 mg, 0.12 mmol), cyclopropylamine (Alfa Aesar, Ward Hill, Mass.; 14 mg, 0.25 mmol) and DIPEA (47 mg, 0.36 mmol) and heating at 100° C. for 1 h. Purification by chromatography (silica gel, 0-100% EtOAc in hexanes followed by 0-10% MeOH in DCM) provided 2′-(3-(cyclopropylamino)-2-methyl-5-quinoxalinyl)-5′,6′-dihydrospiro[cyclopropane-1,7′-pyrrolo[3,2-c]pyridin]-4′(1′H)-one (27 mg, 62% yield) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 11.53 (1H, br s, D2O exch.), 7.95 (1H, dd, J=7.53, 1.47 Hz), 7.58 (1H, dd, J=8.02, 1.37 Hz), 7.42 (1H, dd, J=2.35, 0.59 Hz), 7.36 (1H, br s, D2O exch.), 7.34 (1H, t, J=7.82 Hz), 7.02 (1H, br s, D2O exch.), 3.29 (2H, d, J=2.35 Hz), 2.91 (1H, tq, J=6.75, 3.52 Hz), 2.51 (3H, s), 1.06-1.12 (2H, m), 0.97-1.02 (2H, m), 0.90-0.97 (2H, m), 0.66-0.74 (2H, m). m/z (ESI, +ve) 360.2 (M+H)+.

Provenance & Evidence